Potassium Phosphate, Tribasic → Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate

HRID 2283682노트

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HRID 2283682 반응식
CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:13]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:48]1[C:52]2[CH:53]=[C:54]([O:57][CH3:58])[CH:55]=[CH:56][C:51]=2[S:50][C:49]=1[C:59]([O:61][CH3:62])=[O:60]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:58][O:57][C:54]1[CH:55]=[CH:56][C:51]2[S:50][C:49]([C:59]([O:61][CH3:62])=[O:60])=[C:48]([CH3:13])[C:52]=2[CH:53]=1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 2801561Methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

생성물 1

HCID 12561472Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Methyl boronic acid (120 mg), potassium phosphate (849 mg), water (0.30 ml), palladium acetate (22 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl (95 mg) were added to a solution of methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate (257 mg) in 1,4-dioxane (3.0 ml), and the reaction solution was stirred at 100° C. for 12 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous ammonium chloride solution, an aqueous sodium bicarbonate solution, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate.

후처리

  1. washwashed successively with an aqueous ammonium chloride solution
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated under vacuum
  4. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-ade2f2939fc04385b686a0b1e7d7f253
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145414B2

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